(16S)-17-[(Z)-2-Methyl-2-butenoyloxy]-12beta,16-dihydroxykauran-18-oic acid

Details

• Internal ID: 7766035b-ffc7-49fb-a77d-0d78202a47f0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
• IUPAC Name: (1S,4S,5R,9S,10R,12R,13S,14S)-12,14-dihydroxy-5,9-dimethyl-14-[[(Z)-2-methylbut-2-enoyl]oxymethyl]tetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OCC1(CC23CCC4C(C2CC(C1C3)O)(CCCC4(C)C(=O)O)C)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)OC[C@@]1(C[C@@]23CC[C@H]4[C@]([C@@H]2C[C@H]([C@@H]1C3)O)(CCC[C@@]4(C)C(=O)O)C)O
• InChI: InChI=1S/C25H38O6/c1-5-15(2)20(27)31-14-25(30)13-24-10-7-18-22(3,8-6-9-23(18,4)21(28)29)19(24)11-17(26)16(25)12-24/h5,16-19,26,30H,6-14H2,1-4H3,(H,28,29)/b15-5-/t16-,17+,18-,19-,22+,23+,24-,25+/m0/s1
• InChI Key: LCNRKZPRBJXKGZ-IPKGVIKJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₈O₆
• Molecular Weight: 434.60 g/mol
• Exact Mass: 434.26683893 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.70
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9752	97.52%
Caco-2	-	0.5314	53.14%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7822	78.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8438	84.38%
OATP1B3 inhibitior	+	0.9424	94.24%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7579	75.79%
BSEP inhibitior	+	0.9417	94.17%
P-glycoprotein inhibitior	-	0.6097	60.97%
P-glycoprotein substrate	-	0.6213	62.13%
CYP3A4 substrate	+	0.7043	70.43%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.9015	90.15%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.6817	68.17%
CYP2C19 inhibition	-	0.8591	85.91%
CYP2D6 inhibition	-	0.9400	94.00%
CYP1A2 inhibition	-	0.8899	88.99%
CYP2C8 inhibition	-	0.5571	55.71%
CYP inhibitory promiscuity	-	0.9075	90.75%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7073	70.73%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9568	95.68%
Skin irritation	+	0.5297	52.97%
Skin corrosion	-	0.9582	95.82%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4068	40.68%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9058	90.58%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.4725	47.25%
Acute Oral Toxicity (c)	III	0.4837	48.37%
Estrogen receptor binding	+	0.8421	84.21%
Androgen receptor binding	+	0.6385	63.85%
Thyroid receptor binding	+	0.5451	54.51%
Glucocorticoid receptor binding	+	0.7929	79.29%
Aromatase binding	+	0.7838	78.38%
PPAR gamma	+	0.5177	51.77%
Honey bee toxicity	-	0.7396	73.96%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5255	52.55%
Fish aquatic toxicity	+	0.9897	98.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	97.29%	96.38%
CHEMBL221	P23219	Cyclooxygenase-1	97.21%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.21%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.91%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.13%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.30%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.48%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.08%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.72%	82.69%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.27%	91.07%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.32%	93.00%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	84.70%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.05%	100.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.74%	95.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.39%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.17%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.51%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.27%	95.89%
CHEMBL2664	P23526	Adenosylhomocysteinase	81.93%	86.67%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.55%	85.30%
CHEMBL5408	Q9UHD2	Serine/threonine-protein kinase TBK1	80.42%	90.48%

Plants that contains it

• Asparagus cochinchinensis
• Helianthus atrorubens

Cross-Links

• PubChem: 102056175
• NPASS: NPC34176
• LOTUS: LTS0146804
• wikiData: Q105149919